41838-46-4

Usage

Chemical Properties

Clear colorless to yellow liquid

InChI:InChI=1/C6H14N2/c1-8-4-2-6(7)3-5-8/h6H,2-5,7H2,1H3/p+2

Synthetic route

1-Methyl-4-piperidone (1445-73-4) → 1-methyl-4-aminopiperidine (41838-46-4)

Conditions	Yield
With ammonium formate; palladium on carbon In methanol	100%
With ammonium formate; palladium on activated charcoal In methanol; water at 20℃;	75%
With ammonium formate; palladium on activated charcoal In methanol; water at 20℃;	37%

1-methylpiperidin-4-one hydrochloride (34737-83-2) → 1-methyl-4-aminopiperidine (41838-46-4)

Conditions	Yield
Stage #1: 1-methylpiperidin-4-one hydrochloride With ammonium acetate In methanol for 0.166667h; Stage #2: With sodium cyanoborohydride In methanol for 1h;	88%
With ammonium acetate; sodium cyanoborohydride In methanol for 1.16667h;	88%

C6H12N2 → 1-methyl-4-aminopiperidine (41838-46-4)

Conditions	Yield
With sodium tetrahydroborate at 5℃; for 12h; Reflux; Large scale;	85.3%

N-((4-methylphenyl)methyl)-N-(1-piperidin-4-yl)-4-chlorophenylacetamide (359878-09-4) → 1-methyl-4-aminopiperidine (41838-46-4)

Conditions	Yield
With formic acid; palladium 10% on activated carbon In methanol for 24h; Heating / reflux;	51%

4-(4-methoxybenzylamino)-1-methylpiperidine (359878-55-0) → 1-methyl-4-aminopiperidine (41838-46-4)

Conditions	Yield
With formic acid; palladium 10% on activated carbon In methanol for 24h; Inert atmosphere; Reflux;	51%

1-methyl-piperidin-4-one oxime ; hydrochloride (84540-61-4) → 1-methyl-4-aminopiperidine (41838-46-4)

Conditions	Yield
With ethanol; sodium Heating;	50%

1-methyl-4-piperidinone oxime (1515-27-1) + ethanol (64-17-5) → 1-methyl-4-aminopiperidine (41838-46-4)

Conditions	Yield
With sodium

1-methyl-4-piperidinone oxime (1515-27-1) → 1-methyl-4-aminopiperidine (41838-46-4)

Conditions	Yield
With i-Amyl alcohol; sodium

N-(1-methyl-[4]piperidyl)-acetamide (145344-76-9) → 1-methyl-4-aminopiperidine (41838-46-4)

Conditions	Yield
With hydrogenchloride

1-methylpiperidine-4-carboxamide (62718-28-9) → 1-methyl-4-aminopiperidine (41838-46-4)

Conditions	Yield
With potassium hydroxide; bromine

1-methyl-4-oxo-piperidine-3-carboxylic acid methyl ester (13221-89-1, 56026-45-0) → 1-methyl-4-aminopiperidine (41838-46-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: water; hydrochloric acid 3: isopentyl alcohol; sodium View Scheme

1-Methyl-4-piperidone (1445-73-4) + NH4 OAc → 1-methyl-4-aminopiperidine (41838-46-4)

Conditions	Yield
With hydrogenchloride; NaCNBH3; silica gel In methanol; diethyl ether	3.88 g (88%)
With hydrogenchloride; NaCNBH3; silica gel In methanol; diethyl ether	3.88 g (88%)

4-chlorocarbonyl-4,9-dihydro-1-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one (118306-22-2) → 1-methyl-4-aminopiperidine (41838-46-4) + 4,9-dihydro-1-methyl-4-{[(1-methyl-4-piperidinyl)amino]carbonyl}-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

4-(chlorocarbonyl)-4,9-dihydro-3-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one (118306-21-1) → 1-methyl-4-aminopiperidine (41838-46-4) + 4,9-Dihydro-3-methyl-4-{[(1-methyl-4-piperidinyl)amino]carbonyl}-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

4-(chlorocarbonyl)-4,9-dihydro-1,3-dimethyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one (118306-23-3) → 1-methyl-4-aminopiperidine (41838-46-4) + 4,9-dihydro-1,3-dimethyl-4-{[(1-methyl-4-piperidinyl)amino]carbonyl}-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

1-(trifluoroacetyl)-4-piperidone (65220-86-2) → 1-methyl-4-aminopiperidine (41838-46-4)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium cyanoborohydride; acetic acid / methanol / 20 h / pH ~ 5 1.2: pH ~ 10 2.1: triethylamine / dichloromethane / 0.17 h / 0 °C 2.2: 1.25 h / 0 °C 3.1: potassium carbonate / methanol / 24 h / 40 °C 4.1: formic acid / palladium 10% on activated carbon / methanol / 24 h / Heating / reflux View Scheme

4-(4-methylbenzylamino)-1-(trifluoroacetyl)piperidine (359878-15-2) → 1-methyl-4-aminopiperidine (41838-46-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0.17 h / 0 °C 1.2: 1.25 h / 0 °C 2.1: potassium carbonate / methanol / 24 h / 40 °C 3.1: formic acid / palladium 10% on activated carbon / methanol / 24 h / Heating / reflux View Scheme

2-(4-chlorophenyl)-N-(4-methylbenzyl)-N-(1-trifluoroacetylpiperidin-4-yl)acetamide (359879-83-7) → 1-methyl-4-aminopiperidine (41838-46-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / methanol / 24 h / 40 °C 2: formic acid / palladium 10% on activated carbon / methanol / 24 h / Heating / reflux View Scheme

tert-butyl 4-((4-methylphenyl)methyl)aminopiperidine carboxylate (359877-52-4) → 1-methyl-4-aminopiperidine (41838-46-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 h / 20 °C 1.2: 2 h 2.1: hydrogenchloride / 1,4-dioxane; diethyl ether / 2 h / 20 °C 3.1: formic acid / palladium 10% on activated carbon / methanol / 24 h / Heating / reflux View Scheme

C26H33ClN2O3 → 1-methyl-4-aminopiperidine (41838-46-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / 1,4-dioxane; diethyl ether / 2 h / 20 °C 2: formic acid / palladium 10% on activated carbon / methanol / 24 h / Heating / reflux View Scheme

4-piperidone hydrochloride (41979-39-9) → 1-methyl-4-aminopiperidine (41838-46-4)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: triethylamine / dichloromethane / 0.17 h / 0 °C 1.2: 2 h / 20 °C 2.1: sodium cyanoborohydride; acetic acid / methanol / 20 h / pH ~ 5 2.2: pH ~ 10 3.1: triethylamine / dichloromethane / 0.17 h / 0 °C 3.2: 1.25 h / 0 °C 4.1: potassium carbonate / methanol / 24 h / 40 °C 5.1: formic acid / palladium 10% on activated carbon / methanol / 24 h / Heating / reflux View Scheme

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → 1-methyl-4-aminopiperidine (41838-46-4)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium cyanoborohydride; acetic acid / methanol / 20 h / 20 °C 1.2: 1 h 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 h / 20 °C 2.2: 2 h 3.1: hydrogenchloride / 1,4-dioxane; diethyl ether / 2 h / 20 °C 4.1: formic acid / palladium 10% on activated carbon / methanol / 24 h / Heating / reflux View Scheme

1-methyl-4-aminopiperidine (41838-46-4) + 2‐fluoro‐5‐methoxy‐4‐nitrobenzoic acid (1001345-80-7) → 2-fluoro-5-methoxy-N-(1-methylpiperidin-4-yl)-4-nitrobenzamide (1001345-79-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In ISOPROPYLAMIDE at 18 - 25℃; for 1h;	100%
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl acetamide at 18 - 25℃; for 1h;	100%

1-methyl-4-aminopiperidine (41838-46-4) + 4-amino-3-fluorobenzoic acid (455-87-8) → 4-amino-3-fluoro-N-(1-methylpiperidin-4-yl)benzamide (1001345-97-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 18 - 25℃; for 18h;	100%
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl acetamide at 18 - 25℃; for 18h;	100%

1-methyl-4-aminopiperidine (41838-46-4) + 2-fluoro-4-bromobenzoic acid (112704-79-7) → 4-bromo-2-fluoro-N-(1-methylpiperidin-4-yl)benzamide (893420-55-8)

Conditions	Yield
Stage #1: 4-Amino-1-methylpiperidine; 2-fluoro-4-bromobenzoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1.5h; Stage #2: With sodium hydroxide In water at 20℃;	100%
With triethylamine; HATU In N,N-dimethyl-formamide

1-methyl-4-aminopiperidine (41838-46-4) + 7-(benzyloxy)-2,4-dichloro-6-methoxyquinazoline (60771-18-8) → 7-(benzyloxy)-2-chloro-6-methoxy-N-(1-methylpiperidin-4-yl)quinazolin-4-amine (1197196-50-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;	100%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;	100%
at 20℃;

1-methyl-4-aminopiperidine (41838-46-4) + 5-amino-4-methyl-1-phenyl-1H-pyrazole-3-carboxylic acid (1367870-32-3) → 5-amino-4-methyl-N-(1-methylpiperidin-4-yl)-1-phenyl-1H-pyrazole-3-carboxamide (1610455-25-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 5.5h;	100%

1-methyl-4-aminopiperidine (41838-46-4) + 4-(7-bromo-2,6-dichloro-8-fluoroquinazolin-4-yl)piperazine-1-carboxylic acid tert-butyl ester → tert-butyl 4-(7-bromo-6-chloro-8-fluoro-2-((1-methylpiperidin-yl)amino)quinazolin-4-yl)piperazine-1-carboxylate

Conditions	Yield
With potassium fluoride In dimethyl sulfoxide at 120℃; for 1h;	100%

1-methyl-4-aminopiperidine (41838-46-4) + N-(5-bromo-4-chloropyridin-2-yl)pivalamide (1137477-51-0) → N-(5-bromo-4-(1-methylpiperidin-4-ylamino)pyridin-2-yl)pivalamide (1137477-53-2)

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 220℃; for 3h; Microwave irradiation;	99%

1-methyl-4-aminopiperidine (41838-46-4) + 1-bromo-3-nitro-5-(trifluoromethyl)benzene (630125-49-4) → 1-methyl-N-[3-nitro-5-(trifluoromethyl)phenyl]piperidin-4-amine (1529769-59-2)

Conditions	Yield
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 120℃; Inert atmosphere;	99%
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 120℃; Inert atmosphere;	99%

1-methyl-4-aminopiperidine (41838-46-4) + 4-Bromo-1-fluoro-2-nitrobenzene (364-73-8) → N-(4-bromo-2-nitrophenyl)-1-methylpiperidin-4-amine

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	99%
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 8h;

1-methyl-4-aminopiperidine (41838-46-4) + 6-bromo-4-chloro-3-quinolinecarbonitrile (364793-54-4) → 6-bromo-4-[(1-methylpiperidin-4-yl)amino]quinoline-3-carbonitrile

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 100℃; for 0.5h; Microwave irradiation;	99%

1-methyl-4-aminopiperidine (41838-46-4) + 2-(4-isocyanatophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → N-(1-methyl-piperidin-4-yl)-N'-[4-(4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-yl)-phenyl]-urea (879486-87-0)

Conditions	Yield
In dichloromethane at 20℃; for 5h;	98%
In 1,2-dimethoxyethane

1-methyl-4-aminopiperidine (41838-46-4) + 3-methyl-4-nitrobenzoic acid (3113-71-1) → 3-methyl-N-(1-methyl-4-piperidyI)-4-nitro-benzamide (1001345-96-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 18 - 25℃; for 18h;	98%

1-methyl-4-aminopiperidine (41838-46-4) + 3-chloro-5-hydroxybenzaldehyde (1829-33-0) → 3-chloro-5-{[(1-methylpiperidin-4-yl)amino]methyl}phenol

Conditions	Yield
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 18.5h;	97%

1-methyl-4-aminopiperidine (41838-46-4) + ortho-nitrofluorobenzene (1493-27-2) → N-(1-methyl-piperidin-4-yl)-benzene-1,2-diamine (600725-12-0)

Conditions	Yield
	96%

1-methyl-4-aminopiperidine (41838-46-4) + 5-(1,1-difluoroethyl)-2-methyl-2H-pyrazole-3-carboxylic acid (1024599-54-9) → C13H20F2N4O

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In 1-methyl-pyrrolidin-2-one at 90℃; for 0.166667h; Microwave irradiation;	96%

1-methyl-4-aminopiperidine (41838-46-4) + 3-(cyclopentyloxy)-4-nitrobenzoic acid → 3-(cyclopentyloxy)-N-(1-methylpiperidin-4-yl)-4-nitrobenzamide

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;	96%

1-methyl-4-aminopiperidine (41838-46-4) + methyl 2-isothiocyanatobenzoate (16024-82-1) → 3-(1-methyl-4-piperidyl)-2-thioxo-1H-quinazolin-4-one

Conditions	Yield
With triethylamine In tetrahydrofuran at 150℃; for 0.75h; Microwave irradiation;	96%

1-methyl-4-aminopiperidine (41838-46-4) + 2-Fluoro-5-nitrobenzotrifluoride (400-74-8) → (1-methyl-piperidin-4-yl)-(4-nitro-2-trifluoromethyl-phenyl)-amine (1183289-25-9)

Conditions	Yield
In tetrahydrofuran at 20℃; for 4h;	95%

1-methyl-4-aminopiperidine (41838-46-4) + 5-bromo-2-methoxypyridine-3-carboxaldehyde (103058-87-3) → N-((5-bromo-2-methoxypyridin-3-yl)methyl)-1-methylpiperidin-4-amine

Conditions	Yield
With sodium cyanoborohydride; acetic acid In methanol at 20℃; for 22h;	94%

1-methyl-4-aminopiperidine (41838-46-4) + 3-fluoro-4-nitrobenzoic acid (403-21-4) → 3-fluoro-N-(1-methylpiperidin-4-yl)-4-nitrobenzamide

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;	94%

1-methyl-4-aminopiperidine (41838-46-4) + 3,4,5-Trimethoxybenzoyl chloride (4521-61-3) → 3,4,5-Trimethoxy-N-(1-methyl-piperidin-4-yl)-benzamide

Conditions	Yield
In benzene Ambient temperature;	93%

1-methyl-4-aminopiperidine (41838-46-4) + 4-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carboxylic acid → 4-bromo-N-(1-methylpiperidin-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carboxamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃; for 4h; Inert atmosphere;	92.4%

1-methyl-4-aminopiperidine (41838-46-4) + 4-methyl-benzoyl chloride (874-60-2) → N-(1-methyl-[4]piperidyl)-p-toluamide

Conditions	Yield
In benzene Ambient temperature;	92%

1-methyl-4-aminopiperidine (41838-46-4) + 2-chloro-6,7-dimethoxy-3H-quinazolin-4-one (27631-29-4) → 2-chloro-6,7-dimethoxy-N-(1-methylpiperidin-4-yl)quinazolin-4-amine (1197196-66-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 2h;	92%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 2h;	92%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	90%

1-methyl-4-aminopiperidine (41838-46-4) + 4-nitro-benzoic acid (62-23-7) → N-(1-methylpiperidin-4-yl)-4-nitrobenzamide (210643-97-3)

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;	92%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃;	17.39%
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 35℃; for 4h;

1-methyl-4-aminopiperidine (41838-46-4) + 3‐{[8‐(1‐methyl‐1H‐indol‐6‐yl)quinoxalin‐6‐yl]amino}pyridine‐4‐carboxylic acid → 3‐{[8‐(1‐methyl‐1H‐indol‐6‐yl)quinoxalin‐6‐yl]amino}‐N‐(1‐methylpiperidin‐4‐yl)pyridine‐4‐carboxamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In 1,4-dioxane at 20℃; for 24h;	92%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In 1,4-dioxane at 20℃; for 24h; Inert atmosphere;	92%

1-methyl-4-aminopiperidine (41838-46-4) + ethyl 4-chloro-3-nitrobenzoate (16588-16-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 16h;	92%

1-methyl-4-aminopiperidine + cyclohexanylcarbonyl chloride (2719-27-9) → Cyclohexanecarboxylic acid (1-methyl-piperidin-4-yl)-amide

Conditions	Yield
In benzene Ambient temperature;	91%

1-methyl-4-aminopiperidine (41838-46-4) + 3',4',5'-trimethoxycinnamoyl chloride (10263-19-1) → (E)-N-(1-Methyl-piperidin-4-yl)-3-(3,4,5-trimethoxy-phenyl)-acrylamide

Conditions	Yield
In benzene Ambient temperature;	91%

Upstream product

• 1515-27-1 1-methylpiperidin-4-one oxime 
• 64-17-5 ethanol 
• 145344-76-9 N-(1-methyl-[4]piperidyl)-acetamide 
• 1445-73-4 1-Methyl-4-piperidone 
• 359878-09-4 N-((4-methylphenyl)methyl)-N-(1-piperidin-4-yl)-4-chlorophenylacetamide 
• 13221-89-1 1-methyl-4-oxo-piperidine-3-carboxylic acid methyl ester 
• 34737-83-2 1-methylpiperidin-4-one hydrochloride 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 41979-39-9 4-piperidone hydrochloride 
• 359877-52-4 tert-butyl 4-((4-methylphenyl)methyl)aminopiperidine carboxylate 
• 359879-83-7 2-(4-chlorophenyl)-N-(4-methylbenzyl)-N-(1-trifluoroacetylpiperidin-4-yl)acetamide 
• 359878-15-2 4-(4-methylbenzylamino)-1-(trifluoroacetyl)piperidine 
• 65220-86-2 1-(trifluoroacetyl)-4-piperidone 
• 359878-55-0 4-(4-methoxybenzylamino)-1-methylpiperidine 

Downstream Products

• 830339-06-5 nicotinic acid-(1-methyl-[4]piperidylamide) 
• 1141-58-8 N-(1-methyl-[4]piperidyl)-benzamide 
• 682348-15-8 4-methoxy-benzoic acid-(1-methyl-[4]piperidylamide) 
• 113681-64-4 N-(1-methyl-4-piperidinyl)-5-(aminosulfonyl)-2-methoxybenzamide 
• 110963-39-8 (1-Methyl-piperidin-4-yl)-[1-(2-phenoxy-ethyl)-1H-benzoimidazol-2-yl]-amine 
• 84332-22-9 2-Amino-4-methoxy-pyrimidine-5-carboxylic acid (1-methyl-piperidin-4-yl)-amide 
• 93591-87-8 1-methyl-N-(4-nitrophenyl)piperidin-4-amine 

Relevant academic research and scientific papers

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Compounds of formulae I and II: are disclosed as 5-HT3 inhibitors. Those compounds that exhibit central activity are useful in treating CINV; those that inhibit peripheral receptors are useful to treat IBS-D.

PYRAZOLO[3,4-B]PYRIDINE COMPOUNDS, AND THEIR USE AS PHOSPHODIESTERASE INHIBITORS

The invention relates to a compound of formula (I) or a salt thereof: wherein:R1 is C1-4alkyl, C1-3fluoroalkyl, -CH2CH2OH or -CH2CH2CO2C1-2alkyl;R2 is a hydrogen atom (H), methyl or C1fluoroalkyl;R3 is optionally substituted C3-8cycloalkyl or optionally substituted mono-unsaturated-C5-7cycloalkenyl or an optionally substituted heterocyclic group of sub-formula (aa), (bb) or (cc); in which n1 and n2 independently are 1 or 2; and in which Y is O, S, SO2, or NR10; or R3 is a bicyclic group (dd) or (ee): ; and wherein X is NR4R5 or OR5a. The compounds are phosphodiesterase (PDE) inhibitors, in particular PDE4 inhibitors. Also provided is the use of a compound of formula (I), or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for the treatment and/or prophylaxis of an inflammatory and/or allergic disease in a mammal such as a human, for example chronic obstructive pulmonary disease (COPD), asthma, or allergic rhinitis.